DF1 Questions

Part A – Organic molecules, naming, reactions and mechanisms.
1. Ethanol can be made from ethene in an industrial process.
Give the reagents and conditions required for this reaction.
[3]
2(a). i. Draw, in the boxes below, the full structural formulae for the hydrocarbons propane
and propene.
[1]
ii. Give the term used to describe molecules, such as alkenes, containing a C=C bond.
[1]
(b). Alkenes are also used in drilling oils. Some of these alkenes are structural isomers.
i. Explain the meaning of the term structural isomers.
[1]
ii. Draw the skeletal structures for three alkene isomers of C4H8.
[2]
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3. Which substance will not give 3-methylpentane when reduced with hydrogen?
A 2-ethylbut-1-ene
B 3-methylpent-2-ene
C 2-methylpent-1-ene
D 3-methylpent-1-ene
Your answer [1]
4. Which substance cannot be made in a single step from C2H4?
A C2H5OH
B C2H5Br
C C2H6
D C2H5NH2
Your answer [1]
5. Anaesthetics used in the mid-19th century included dinitrogen oxide, N 2O (laughing gas) and
ethoxyethane (C2H5)2O.
i. Draw the skeletal formula for ethoxyethane and name the homologous series to
which it belongs.
homologous series ........................................................... [2]
ii. Compound A is a structural isomer of ethoxyethane.
Name compound A and give its molecular formula.
Compound A
name ..............................................................................................
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molecular formula ...........................................................................
[2]
iii. One form of compound A is represented by the structure below.
Explain the significance of the ‘wedge’ bond.
[1]
6. When but-1-ene, CH3CH2CH=CH2, reacts with ICl the main product is 1-iodo-2-chlorobutane,
CH3CH2CHCl CH2I.
Suggest a mechanism for this reaction.
Show full and partial charges and ‘curly arrows’.
[3]
7. How many structural isomers of C5H10 show E/Z isomerism?
A. 1
B. 2
C. 3
D. 4
Your answer
[1]
8. Which term correctly describes cyclohexane?

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A Arene
B Alkene
C Aliphatic
D Unsaturated
Your answer [1]
9
(c). Hexa-2,4-diene, CH3CH=CHCH=CHCH3, can form several E / Z isomers.
i. Give two reasons why E/Z isomers exist.
[2]
ii. Draw structural diagrams to represent all the E / Z isomers.

Label the appropriate parts of each formula with E or Z.
[4]
10. The smell of burning fat is caused mainly by the presence of ‘acrolein’. This is formed by the
decomposition of propane-1,2,3-triol from the fat.
Acrolein is a colourless liquid that has many uses in organic chemistry.

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Acrolein also occurs in cigarette smoke and is the main carcinogenic agent.
How could a sample of cigarette smoke be tested for the presence of unsaturated
compounds? Indicate the positive result of the test.
[1]
11.
i. How many σ and π bonds are there in a propene molecule?
Number of σ bonds Number of π bonds

ii. Propene has a H–C–H bond where the C atom forms a double bond.
What is the bond angle of this H–C–H bond?
12(a). The substance anethole is present in some alcoholic drinks such as ‘ouzo’. Alcoholic drinks
containing anethole go cloudy when water is added.
i. Give the molecular formula of anethole.
[1]
ii. Name the saturated functional group in anethole.
[1]
iii. Naturally occurring anethole is an E isomer.
Draw the structure of the E isomer.

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[1]
(b). The double bond in anethole reacts with bromine.
Draw the skeletal formula of the compound produced.
[1]
(c). i. Give the mechanism of the reaction of bromine with ethene, showing whole and
partial charges, curly arrows, and the final product.
[3]
ii. Ethene is brominated using aqueous bromine.
Suggest why CH2OHCH2Br is formed but CH2OHCH2OH is not formed.
[2]
13(a). Poly(phenylethene), commonly known as ‘polystyrene’, can be used to make packaging.

The monomer phenylethene is shown below.

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Phenylethene is polymerised in the laboratory. Any unreacted phenylethene can be detected
by adding aqueous bromine to the reaction mixture. Bromine reacts to produce compound A.
i. What colour change would be observed when phenylethene reacts with aqueous
bromine?
[1]
ii. The first step in the mechanism for the reaction of phenylethene with bromine is
shown below.
What name is given to the type of organic intermediate, such as intermediate 1,

formed in the reaction?
[1]
iii. If an aqueous mixture of bromine and potassium chloride is added to phenylethene,

some of compound B is produced, as well as compound A.

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Use the mechanism shown in (c)(ii) to explain why both compound A and compound
B are formed.
[1]
(b). Another substituted alkene is 1-chloroprop-1-ene, shown below
Unlike phenylethene,1-chloroprop-1-ene shows E/Z stereoisomerism.
Describe how this E/Z isomerism arises.
[2]

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14. There are several structural isomers with the formula C8H10.
Two of these are shown below, labelled Compound F and Compound G.
i. Underline the name below that correctly describes these molecules.
alkane arene cycloalkane alkene
[1]
ii. Using the same type of formula, draw another structural isomer of C 8H10 containing
an aromatic ring.
[1]
15. Butene, C4H8, is a minor component in crude oil. Butene is used in co-polymerisation with
other monomers to form hot melt adhesives.
There are structural isomers of C4H8. One of the structural isomers is but-2-ene.
But-2-ene is an isomer of C4H8 that exhibits stereoisomerism.
Draw the structures of both stereoisomers of but-2-ene and give their systematic
names.
nam
e:

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nam
e:
[2]
16(a). ‘Isobutylene’ is an important hydrocarbon, used to make some petrol additives.

The skeletal formula of isobutylene is shown below.
Give the systematic name for isobutylene.

[1]
(b). Isobutylene has a structural isomer that shows E/Z isomerism.

Draw the Z isomer.
[1]
17(a). Some students have two isomeric compounds A and B with the molecular formula C9H10O.
They are both used in the perfume industry.
The students do some tests to find out which functional groups are present.
They look at the formulae and decide that the molecules are probably unsaturated due to
the low proportion of hydrogen.
They test each compound with bromine water.
Both compounds A and B show a positive result with bromine water.
Describe the colour change the students would see in the reaction.
[1]

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(b). They then decide that the molecules could be aromatic.
What does aromatic mean?

[1]
18(a). A perfume laboratory is investigating the molecules responsible for the smell of some
common flowers.
Their investigations suggest that the following two liquid compounds are important in the
characteristic smell of hyacinth flowers.
Ocimenol and cinnamyl alcohol are both unsaturated molecules.
Explain how you could use a solution of bromine water to show which of the molecules has
the greater degree of unsaturation.
[4]
(b). Both ocimenol and cinnamyl alcohol molecules show stereoisomerism.
• Name the type of stereoisomerism shown by these molecules.

• Explain how this isomerism arises.
The structure of one of the stereoisomers of cinnamyl alcohol is shown in the left hand
•
box below; draw the structure of the other isomer in the right hand box.
Type of
stereoisomerism

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Explanation
[3]
19. Some students are given samples of two liquid hydrocarbons, B and C, to test as fuels.
Molecula Aliphatic or Saturated or

Fuel Name Skeletal formula
r formula aromatic? unsaturated?
Cyclohexan
B
e
C C7H16
Complete the table above, filling the empty boxes.
[3]
20. Most reactions of ethene are addition reactions. The diagram below shows step 1 of the
mechanism for the reaction of ethene with bromine.
Mechanism 2.1
i. Give the name of the type of intermediate, such as intermediate A, that forms in this
reaction.

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[1]
ii. The reaction in step 1 involves attack by an electrophile.
Explain what is meant by the term electrophile.
[2]
iii. A scientist reacts ethene with bromine in a solution that also contains sodium
chloride. Two of the products that form are CH2BrCH2Br and CH2ClCH2Br.
Use Mechanism 2.1 to explain why these two products form.
[3]
21. CH3CH=CHCH3 exists as two stereoisomers.
Draw structures of the two stereoisomers and give their systematic names.

page.
[3]

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Part B – Cracking and heterogeneous catalysis
22. Alkenes are important in the chemical industry. Simple alkenes occur naturally and form a
small percentage of the hydrocarbons in crude oil.
About 10% of crude oil is converted into alkenes by the process of catalytic cracking.
i. Write the equation for the cracking of decane to produce ethene and one other
product.
Use molecular formulae in your equation.
[1]
ii. Heterogeneous catalysts are used in cracking.
Explain, in the context of catalysis, the term heterogeneous and describe the first
stage in the mechanism of this type of catalysis.
In your answer, you should use appropriate technical terms, spelled correctly.
[2]
iii. The structure of ethane can be represented by the diagram below.
Explain the significance of the wedges and dotted lines in this structure.
[1]

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23.
Propene, C3H6, can be made by cracking longer-chain hydrocarbons.
i. Write the equation for the cracking of nonane to give two molecules of propene and
one other molecule.
ii. What mass of propene (in kg) would be obtained from 15 kg of nonane in the reaction
in (i) if the percentage yield was 85%?
mass of propene
=
24. Catalytic cracking of hydrocarbons is carried out in the petrochemical industry.

Hot vaporised hydrocarbons and a powdered catalyst are fed into the bottom of a tube and
forced upwards by steam.
A student wishes to crack a sample of liquid decane in the laboratory and collect the
gaseous products.
Fig. 1.1 shows the apparatus that a student drew before doing this.
What modifications would be required for this apparatus to work?
Explain your answers.
Fig. 1.1

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[4]
25. Ethene, C2H4, is the simplest alkene and has a wide variety of uses in industry, especially in
making polymers.
Ethene is made by the catalytic cracking of longer hydrocarbons, such as those in light
naphtha.
Some students are given a supply of liquid light naphtha and they need to obtain some
ethene from it. They use aluminium oxide as the catalyst.
i. Draw a labelled diagram of a suitable apparatus that they could use.
ii. They test the gas by shaking it with some aqueous bromine.
Describe the colour change that they would see.
[1]
26. One model explaining the function of a heterogeneous catalyst uses some or all of the
following steps:
1. intramolecular bonds weaken and break

2. product molecules desorb off the catalyst surface
3. reactant molecules adsorb onto catalyst surface
4. new bonds form
5. intermolecular bonds weaken and break
What is the correct order of appropriate steps for this model?
A. 1 → 5 → 4 → 3
B. 3 → 1 → 4 → 2
C. 3 → 4 → 5 → 2
D. 3 → 5 → 4 → 2

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Your answer
[1]
27. Zeolites are microporous, sponge-like materials, developed from naturally occurring
minerals. They have an enormous range of applications.
Zeolites can be used as heterogeneous catalysts in the cracking of crude oil.
i. Explain the terms heterogeneous and catalyst.
[2]
ii. Write an equation, using molecular formulae, for the cracking of decane to produce
an alkene with three carbon atoms and one other product.
[1]

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Part C – Enthalpy experiments
28(a). Many children's science kits contain the chemicals ‘sodium bicarbonate’, NaHCO 3, and
‘citric acid’, C6H8O7. If solid sodium bicarbonate is added to a solution of citric acid, the
resulting evolution of gas can be used to ‘power’ small toys such as boats and cars.
A student decides to measure the enthalpy change for this reaction using the apparatus
below.
The student adds 12 g of sodium bicarbonate to excess citric acid solution.

The results are given below.
Mass of solution formed = 25.0 g

Starting temperature of solution = 22 °C
Finishing temperature of solution = 6 °C
i. Calculate the energy transferred from the solution.
The solution has a specific heat capacity of 4.18 J g−1 K−1.
energy transferred = ........................................................... J [1]
ii. Calculate the enthalpy change, ΔH, per mole of sodium bicarbonate in this reaction.
Give your answer, in kJ, to two significant figures.
ΔH = ........................................................... kJ mol−1[3]
iii. The answer calculated in (ii) is different from the value quoted in data books.
Suggest one limitation in the practical procedure which would lead to the difference.
[1]

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29. Hydrogen iodide reacts with a solution of barium hydroxide.
2HI + Ba(OH)2 → BaI2 + 2H2O Equation 20.3
A student places 20.0 cm3 of 2.0 mol dm−3 HI (aq) (an excess) in a polystyrene cup. The
temperature is measured every minute. 2.0 g of barium hydroxide powder is added after two
minutes. The student obtains the following results.
Time / min Temperature / °C

0 23.5
1 23.5
3 29.0
4 35.5
5 37.0
6 36.5
7 35.8
8 34.8
9 34.7
10 33.7
i. Plot a graph of these results to determine an accurate value for the temperature rise.

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temperature rise = ............................. °C [4]
ii. Calculate the enthalpy change of neutralisation, ΔneutH, for the reaction in Equation
20.3.
Assume that the density and specific heat capacity of the solution are the same as
those for the water.
ΔneutH = ............................. kJ mol−1 [3]
iii. The volume of HI is measured using a burette that can be read to ±0.05 cm 3.
Calculate the uncertainty in this measurement.

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uncertainty = ............................. % [1]
30(a). A student investigates the use of spirit burners as alternative heating sources for
laboratories without a gas supply.
A spirit burner containing ethanol is weighed. 100 cm3 of water are measured into a beaker
clamped above the spirit burner. The temperature of the water is recorded. The spirit burner
wick is lit and allowed to heat the water. The thermometer is used to stir the water. After
about 5 minutes the flame of the burner is extinguished, the maximum temperature reached
by the water is recorded and the spirit burner is re-weighed.
The student records the following results.
Mass of spirit burner and ethanol before burning / g 20.33

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Mass of spirit burner and ethanol after burning / g 18.92
o
Initial temperature of the water / C 17.5
Maximum temperature reached by the water / oC 88.0
i. The student repeats the experiment using a spirit burner containing methanol
instead of ethanol. The same mass of fuel is burned in both experiments.
Suggest two reasons why the total energy transferred from the spirit burner is
different in the two experiments.
[2]
ii. Describe how the student can ensure that the same amount of energy is transferred
from the spirit burner in the experiment using methanol as is transferred in the
experiment described in (a)(ii).
State the assumption you have made.
[2]
(b). At the end of the experiments the student notices that there is a black deposit on the
bottom of the beaker.
Suggest what this might be and why it might have been formed.
[2]
31(a). Disposable lighters use butane (C4H10). Heat energy is released when the butane is burned.
Some students wish to determine the enthalpy change of combustion (ΔcH) of butane. They
use the apparatus below.

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The mass of the lighter is measured before the butane is ignited and again after the butane
has burned.
The water is stirred continuously using the thermometer and the temperature of the water
in the metal can is measured before and after the combustion of the butane.
The results are shown below.
mass of lighter and butane before combustion 14.86 g

mass of lighter after combustion 14.39 g
temperature of water before heating 19 °C
temperature of water after heating 74 °C
mass of water 50.00 g
Table 1.1
Write a chemical equation to represent the standard enthalpy change of combustion of

butane (ΔcH⊖).
Show state symbols.
[2]
(b). Calculate a value for the enthalpy change of combustion (in kJ mol −1) of butane (ΔcH) using
the experimental results in Table 1.1.
enthalpy change of combustion of butane, ΔcH =

........................................................... kJ mol−1[3]

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(c). The standard enthalpy changes of combustion of some alkanes are given in the table below.
Alkane ΔcH⊖/kJ mol−1

CH4 −890
C2H6 −1560
C3H8 −2220
C5H12 −3509
C6H14 −4194
i. Estimate the standard enthalpy change of combustion of butane.
ΔcH⊖ = ........................................................... kJ mol−1[1]
ii. Suggest two reasons, apart from ‘heat losses’, why the value calculated in the simple
experiment in (b) is much less exothermic than the value estimated.
1
[2]
iii. The students repeat the experiment using the same thermometer and balance.
State and explain one way in which they could modify the procedure in order to
obtain a more accurate value for the enthalpy change of combustion of butane.
[1]

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32 Some students are given samples of two liquid hydrocarbons, B and C, to test as fuels.
.
Molecular Aliphatic or Saturated or
Fuel Name Skeletal formula
formula aromatic? unsaturated?
B Cyclohexane
C C7H16
Students burn different fuels separately in the apparatus shown below.

Their aim is to compare the energies produced on combustion.
i. State the measurements that the students would make to calculate a value for the energy
produced. Show how these measurements would be used to calculate this energy.
[2]
ii. State and explain two improvements that could be made to increase the accuracy of the
calculated value of the energy produced.
[4]
2

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[4]
33(a). Long chain alkanes can be cracked to provide better fuels and raw materials for the
chemical industry. One such cracking reaction is shown in equation 31.1.
C12H26 → 2C3H6 + C6H14 Equation 31.1
Some students want to investigate the usefulness of hexane as a fuel.
i. Describe an experiment they could use to determine the enthalpy change of

combustion of liquid hexane in the laboratory.
[1]
ii. Show how the result would be calculated from the measurements made when
carrying out the experiment in part (i).
[1]
iii. Describe two ways in which the students could make the basic experiment more
accurate.
2
[2]

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34. A group of students investigates the exothermic reaction between zinc and copper sulfate
solution.
Zn(s) + CuSO4(aq, 0.2 mol dm–3) → Cu(s) + ZnSO4(aq)
i. The students are provided with powdered zinc metal and solid CuSO 4•5H2O (Mr =
250).
They measure the temperature rise when 100 cm3 (an excess) of 0.2 mol dm–3 copper
sulfate is used.
Design a suitable method to investigate this exothermic reaction.
[5]
ii. The students repeat the experiment, measuring the temperature at different times.
They plot the graph shown.

page.
Use the graph to make an accurate measure of the temperature rise.
Show your working on the graph.
temperature rise = .................................................... °C [2]
END OF QUESTION PAPER

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Part A – Organic molecules, naming, reactions and mechanisms.

1. Ethanol can be made from ethene in an industrial process.

Give the reagents and conditions required for this reaction.

i. Explain the meaning of the term structural isomers.

© OCR 2022. You may photocopy this

Your answer [1]

4. Which substance cannot be made in a single step from C2H4?

Your answer [1]

homologous series ........................................................... [2]

ii. Compound A is a structural isomer of ethoxyethane.

Name compound A and give its molecular formula.

iii. One form of compound A is represented by the structure below.

Explain the significance of the ‘wedge’ bond.

Show full and partial charges and ‘curly arrows’.

7. How many structural isomers of C5H10 show E/Z isomerism?

8. Which term correctly describes cyclohexane?

© OCR 2022. You may photocopy this

Your answer [1]

i. Give two reasons why E/Z isomers exist.

ii. Draw structural diagrams to represent all the E / Z isomers.

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i. How many σ and π bonds are there in a propene molecule?

Number of σ bonds Number of π bonds

What is the bond angle of this H–C–H bond?

i. Give the molecular formula of anethole.

ii. Name the saturated functional group in anethole.

iii. Naturally occurring anethole is an E isomer.

Draw the structure of the E isomer.

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(b). The double bond in anethole reacts with bromine.

Draw the skeletal formula of the compound produced.

ii. Ethene is brominated using aqueous bromine.

Suggest why CH2OHCH2Br is formed but CH2OHCH2OH is not formed.

13(a). Poly(phenylethene), commonly known as ‘polystyrene’, can be used to make packaging.

© OCR 2022. You may photocopy this

What name is given to the type of organic intermediate, such as intermediate 1,

iii. If an aqueous mixture of bromine and potassium chloride is added to phenylethene,

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(b). Another substituted alkene is 1-chloroprop-1-ene, shown below

Unlike phenylethene,1-chloroprop-1-ene shows E/Z stereoisomerism.

Describe how this E/Z isomerism arises.

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i. Underline the name below that correctly describes these molecules.

alkane arene cycloalkane alkene

But-2-ene is an isomer of C4H8 that exhibits stereoisomerism.

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16(a). ‘Isobutylene’ is an important hydrocarbon, used to make some petrol additives.

Give the systematic name for isobutylene.

(b). Isobutylene has a structural isomer that shows E/Z isomerism.

They test each compound with bromine water.

Both compounds A and B show a positive result with bromine water.

© OCR 2022. You may photocopy this

What does aromatic mean?

Ocimenol and cinnamyl alcohol are both unsaturated molecules.

(b). Both ocimenol and cinnamyl alcohol molecules show stereoisomerism.

• Name the type of stereoisomerism shown by these molecules.

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Molecula Aliphatic or Saturated or

Complete the table above, filling the empty boxes.

© OCR 2022. You may photocopy this

ii. The reaction in step 1 involves attack by an electrophile.

Explain what is meant by the term electrophile.

Use Mechanism 2.1 to explain why these two products form.

21. CH3CH=CHCH3 exists as two stereoisomers.